Application of a process friendly morpholine synthesis to (S,S)-Reboxetine

被引:19
作者
Assaf, Georges [1 ]
Cansell, Gemma [1 ]
Critcher, Doug [1 ]
Field, Stuart [1 ]
Hayes, Stewart [1 ]
Mathew, Suju [1 ]
Pettman, Alan [1 ]
机构
[1] Pfizer Ltd, Dept Chem Res & Dev, Sandwich CT13 9NJ, Kent, England
关键词
REDUCTIVE CLEAVAGE; ACETALS; KETALS; ETHERS;
D O I
10.1016/j.tetlet.2010.07.106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report our results on the construction of a morpholine ring system from the corresponding epoxide and amino alcohol. From this study, we were able to convert a previous four-step synthesis into a more efficient two-step process. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5048 / 5051
页数:4
相关论文
共 13 条
[1]  
[Anonymous], 2010, WIPO (PCT) Patent, Patent No. [2010044016, WO2010044016A1]
[2]   The synthesis and biological activity of 1-alkyl-4-(3-azacyclobenzoyl)-5-hydroxypyrazole herbicides [J].
Benko, Z ;
Shinkle, S ;
Van Heertum, J ;
Jackson, J ;
McQuiston, J ;
Webster, J ;
Turner, J ;
Weimer, M ;
Paterson, E .
CHIMIA, 2003, 57 (11) :720-724
[3]   SYNTHESIS AND RESOLUTION OF THE NOVEL APPETITE-SUPPRESSANT 2-BENZYLMORPHOLINE, A NONSTIMULANT ISOMER OF PHENMETRAZINE [J].
BROWN, GR ;
FORSTER, G ;
FOUBISTER, AJ ;
STRIBLING, D .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1990, 42 (11) :797-799
[4]   Critical assessment of pharmaceutical processess - A rationale for changing the synthetic route [J].
Butters, Mike ;
Catterick, David ;
Craig, Andrew ;
Curzons, Alan ;
Dale, David ;
Gillmore, Adam ;
Green, Stuart P. ;
Marziano, Ivan ;
Sherlock, Jon-Paul ;
White, Wesley .
CHEMICAL REVIEWS, 2006, 106 (07) :3002-3027
[5]   Catalytic reductive etherification of ketones with alcohols at ambient hydrogen pressure: A practical, waste-minimized synthesis of dialkyl ethers [J].
Goossen, Lukas J. ;
Linder, Christophe .
SYNLETT, 2006, (20) :3489-3491
[6]   Convenient two-step conversion of lactones into cyclic ethers [J].
Hansen, MC ;
Verdaguer, X ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2360-2361
[7]   Process development for (S,S)-reboxetine succinate via a sharpless asymmetric epoxidation [J].
Henegar, Kevin E. ;
Cebula, Mateusz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :354-358
[8]   Process development and scale-up for (±)-reboxetine mesylate [J].
Henegar, Kevin E. ;
Ball, Cynthia T. ;
Horvath, Carolyn M. ;
Maisto, Keith D. ;
Mancini, Sarah E. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :346-353
[9]   CATALYSIS BY SOLID SUPERACIDS .20. NAFION-H CATALYZED REDUCTIVE CLEAVAGE OF ACETALS AND KETALS TO ETHERS WITH TRIETHYLSILANE [J].
OLAH, GA ;
YAMATO, T ;
IYER, PS ;
PRAKASH, GKS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2826-2828
[10]  
RONALD M, 2007, BIOORG MED CHEM LETT, V17, P533